Sodium Hydroxide → (Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid

HRID 1110499Notes

Reaction equation

HRID 1110499 reaction equation
C([O:3][C:4](=[O:23])/[CH:5]=[CH:6]\[CH:7]=[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])C.[OH-].[Na+]>CO>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])=[CH:7]/[CH:6]=[CH:5]\[C:4]([OH:23])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86742561(Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347237(Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acidYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrolysis of (Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester (0.4 g) in methanol (5 mL) was carried out as before using 4N sodium hydroxide (0.6 mL). After acidification, the product was extracted into dichloromethane (2×30 mL). The combined dried extracts were evaporated and the residue crystallized from ether-hexane to yield 0.35 g of (Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid mp 147°-148° C. Anal. Calculated for C17H12F2O2 : C, 71.32; H. 4.22; F, 13.27 Found: C, 71.36; H, 4.31; F. 13.52.

Workup

  1. extractionAfter acidification, the product was extracted into dichloromethane (2×30 mL)
  2. customThe combined dried extracts
  3. customwere evaporated
  4. customthe residue crystallized from ether-hexane

Sources & evidence

ORD record
ord-d103a0456f2442bfa7d197ce1dd7f600
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

Loading…